Synthesis of Indenopyridine Derivatives via MgI2-Promoted [2+4] Cycloaddition Reaction of In-situ Generated 2-Styrylmalonate from Donor-Acceptor Cyclopropanes and Chalconimines

被引:31
作者
Verma, Kamal [1 ]
Banerjee, Prabal [1 ]
机构
[1] Indian Inst Technol Ropar, Dept Chem, Nangal Rd, Rupnagar 140001, Punjab, India
关键词
2-styrylmalonate; donor-acceptor cyclopropanes; indenopyridine; chalconimines; DIELS-ALDER REACTIONS; POTENTIAL ANTIDEPRESSANTS; MJ-III-65; NSC-706744; 4+2 ANNULATION; ROUTE; COMPLEXES; ANALOGS;
D O I
10.1002/adsc.201800598
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An unexpected MgI2-promoted [2 + 4] cycloaddition reaction of in-situ generated 2-styrylmalonate from donor-acceptor cyclopropanes with chalconimines to synthesize highly substituted indenopyridine derivatives under the mild reaction conditions have been developed. Additionally, these derivatives were utilized for the synthesis of highly substituted 9-membered lactam by oxidative C=C bond cleavage and spiro [oxoindane-pyrrolidine] derivative via Meinwald type rearrangement.
引用
收藏
页码:3687 / 3692
页数:6
相关论文
共 50 条
[1]   Cellular topoisomerase I inhibition and antiproliferative activity by MJ-III-65 (NSC 706744), an indenoisoquinoline topoisomerase I poison [J].
Antony, S ;
Kohlhagen, G ;
Agama, K ;
Jayaraman, M ;
Cao, SS ;
Durrani, FA ;
Rustum, YM ;
Cushman, M ;
Pommier, Y .
MOLECULAR PHARMACOLOGY, 2005, 67 (02) :523-530
[2]  
Antony S, 2003, CANCER RES, V63, P7428
[3]   RELATIONSHIP BETWEEN ANTIHISTAMINE AND ANTIDEPRESSANT ACTIVITY IN HEXAHYDROINDENOPYRIDINES [J].
AUGSTEIN, J ;
LEEMING, PR ;
HAM, AL .
JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (05) :466-&
[4]   Formal Insertion of Thioketenes into Donor-Acceptor Cyclopropanes by Lewis Acid Catalysis [J].
Augustin, Andre U. ;
Busse, Marius ;
Jones, Peter G. ;
Werz, Daniel B. .
ORGANIC LETTERS, 2018, 20 (03) :820-823
[5]   Synthesis and Biological Evaluation of New Carbohydrate-Substituted Indenoisoquinoline Topoisomerase I Inhibitors and Improved Syntheses of the Experimental Anticancer Agents Indotecan (LMP400) and Indimitecan (LMP776) [J].
Beck, Daniel E. ;
Agama, Keli ;
Marchand, Christophe ;
Chergui, Adel ;
Pommier, Yves ;
Cushman, Mark .
JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (04) :1495-1512
[6]   INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF N-SULFONYL ALPHA,BETA-UNSATURATED IMINES - A GENERAL-APPROACH TO IMPLEMENTATION OF THE 4-PI PARTICIPATION OF 1-AZA-1,3-BUTADIENES IN DIELS-ALDER REACTIONS [J].
BOGER, DL ;
CORBETT, WL ;
CURRAN, TT ;
KASPER, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1713-1729
[7]   DIELS-ALDER REACTIONS OF AZADIENES [J].
BOGER, DL .
TETRAHEDRON, 1983, 39 (18) :2869-2939
[8]   Styrylmalonates as an Alternative to Donor-Acceptor Cyclopropanes in the Reactions with Aldehydes: A Route to 5,6-Dihydropyran-2-ones [J].
Borisov, Denis D. ;
Novikov, Roman A. ;
Eltysheva, Anna S. ;
Tkachev, Yaroslav V. ;
Tomiloy, Yury V. .
ORGANIC LETTERS, 2017, 19 (14) :3731-3734
[9]   Heterocycles from cyclopropanes: applications in natural product synthesis [J].
Carson, Cheryl A. ;
Kerr, Michael A. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3051-3060
[10]   Intramolecular donor-acceptor cyclopropane ring-opening cyclizations [J].
Cavitt, Marchello A. ;
Phun, Lien H. ;
France, Stefan .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (03) :804-818